


Awful Awkward Awesome

by frozen_delight



Category: Supernatural
Genre: Awkward Sexual Situations, Bad Sex, First Time, M/M
Language: English
Status: Completed
Published: 2016-03-27
Updated: 2016-03-27
Packaged: 2018-05-29 11:32:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,768
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6373066
Author URL: https://archiveofourown.org/users/frozen_delight/pseuds/frozen_delight
Summary: <blockquote class="userstuff">
              <p>Written for the prompt: “Sam likes to slam his lovers into the walls, leave bruises on their skin, bite marks on their neck. Dean likes to spread his lovers out in front of him, spend hours worshiping their bodies. When Sam and Dean finally get together, they're both shocked by how the other person has sex.”</p>
            </blockquote>





	Awful Awkward Awesome

**Author's Note:**

  * Translation into 中文 available: [【翻译】Awful Awkward Awesome](https://archiveofourown.org/works/6485650) by [katze_k](https://archiveofourown.org/users/katze_k/pseuds/katze_k)



> Unbetaed, apologies for any mistakes.
> 
> Happy Easter to those of you who celebrate it! <3

In Dean’s experience, sex is awesome. Like, really really awesome.  
  
He’s also come to believe that sex with him is pretty awesome. _Best night of my life Dean._ It’s a phrase he’s heard more than once.  
  
As for Sam—he’s amazingly fit, knows Dean better than anyone and happens to be seriously hot once he’s not hiding behind his bangs and fifty dusty old books. So of course the idea of having sex with Sam seems pretty damn awesome too.  
  
Which is why Dean’s perfectly unprepared for the disaster about to unfold when Sam comes to his room, a look of determination on his face.  
  
“Sammy,” Dean says, and thinks, _finally_.  
  
‘Cause it’s taken them for-friggin’-ever to get to this point.  
  
“I wanna spend the rest of my life with you,” Sam had told him during their research on a haunting in New Hope, Pennsylvania. “In whatever way you’ll have me.”  
  
Or some sappy shit like that.  
  
Instead of laughing at him, like a good big brother woulda done, Dean had assured Sam he wanted him in every single way.  
  
His heart hammered against the roof of his mouth as Dean waited for Sam’s reaction. He found himself thinking that this new total honesty policy between them might actually pay off. But Sam only gave him a bashful smile and returned his attention to the casefiles in front of him.  
  
After they’d closed the case, arrived back at the bunker and still nothing had happened, Dean began to consider that maybe there was more to Sam’s reluctance to take the next step than his admirable work ethics. The only thing that indicated Sam even wanted to take things further was his insistence they both get tested.  
  
Nothing wrong with that. Dean was a champion of safer sex, and if Sam wanted to do it bare, Dean could get behind that too, pun intended.  
  
But after their results had arrived—negative, as expected—and still nothing happened, Dean grew restless. What the fuck was his dainty princess of a brother waiting for? Flowers and a ring?  
  
Thankfully, before Dean could fret himself to death, Sam dropped the bizarre eunuch act. ‘Cause that look on Sam’s face right here—Dean’s seen it on hundreds of faces, in hundreds of bars, and it only ever means one thing.  
  
For all his restraint during the past few weeks, Sam wastes no time now. His hands land on Dean’s hips, steering him backwards, while his mouth connects with Dean’s.  
  
Wow, thinks Dean as his back hits the wall. Kissing. He loves kissing.  
  
Except—what Sam’s doing… Wow, Dean thinks again, this time not so much in aroused amazement as in pure, unadulterated shock. Whatever this is, kissing it ain’t. Honestly, is Sam trying to chew off his lips?  
  
“Hey Sammy,” he says, pushing his brother away with what he hopes is a mostly encouraging smile and not a total mood killer. “I’m kinda fond of this face, ‘kay?”  
  
“Okay,” Sam agrees, chest heaving, eyebrows slowly climbing towards his hairline. It’s cute.  
  
“So—don’t eat it?”  
  
For a moment, Sam stares at him, puzzled. Then his face morphs into an easy grin. “No problem.” If Dean thought the frown was cute, it’s nothing next to the force of Sam’s dimples.  
  
He can’t wait for Sam to close the space between them again, so he wraps his hands around Sam’s neck and hauls him back in. Sam follows him willingly. This time he avoids Dean’s face. Instead, his mouth latches itself onto Dean’s collarbone. Meanwhile, his hands wrap themselves around Dean’s head and neck. They’re warm and freaking huge. Huh. This is nice. It makes Dean feel safe, protected, loved.  
  
But before he can really get into it, Sam’s hands yank his head here and there. Unless Dean’s somehow missed the memo and this is a new tantric massage technique, Sam’s trying to snap his neck. And—ow! There goes the skin on his back! Who the hell mind-whammied Sam enough to believe it’s sexy to drag someone across a scraping surface? It hurts like a bitch.  
  
He pushes Sam away again. “What d’you think you’re doin’?” Not exactly subtle, okay, but who cares about subtle when their back feels like it’s on fire?  
  
Sam looks at him with wide, confused puppy eyes. “Uh—kissing you?”  
  
“Kiss—” There’s a hysterical edge to Dean’s laugh, sue him. “Dude, I think you got ‘kissing’ confused with ‘being trapped inside a meat grinder’!”  
  
Sam’s shoulders droop, dejected. It reminds Dean of the doleful albatross that graced the cover of the alphabet book Bobby gave him for his sixth birthday. A lump forms at the back of his throat.  
  
“I—sorry.” He waves a hand between them. “This is just so weird, man.”  
  
The hint of a smile returns to Sam’s face. “Tell me about it.”  
  
“So…uh…bed?” He gestures behind him.  
  
For a beat or two Sam remains doubtful, then he nods. “Sure.” In a flash, he strips off his clothes.  
  
Dean can only gape at him—and not because Sam looks stunning. (Though he does.) He’s still fumbling with his shirt buttons. “This a race I don’t know ‘bout?”  
  
“Come on, old man.” Sam stalks towards him in all his naked, muscled glory and wrenches at Dean’s shirt.  
  
“Careful!” Dean bats his hands away. “This is one of my favorites.”  
  
“Okay,” Sam says somewhat meekly, and Dean feels bad again, though not bad enough to regret saving his shirt from sure destruction.  
  
Things considerably improve once he’s got Sam spread out on his bed and can worship him to his heart’s content. And fuck, there’s a _lot_ to be worshipped. The well-defined, gleaming pecs. The narrow, sharp hips. The strong thighs. The shoulders, nowhere near as ginormous as they used to be before Sam’s shoulder injury, but oh so firm and reliable. Last but not least, the straining, more than proportional cock.  
  
It’s not like Dean’s never had the opportunity to touch pretty much every single inch of Sam’s skin. But usually that involved panic, whiskey, dental floss and a fuckload of blood. So this—getting to touch and taste all of Sam without fear or hurry or any higher purpose but pleasure—it’s a fuckin’ luxury, that’s what.  
  
As Dean slowly kisses his way from Sam’s wrist to his collarbone, devoting particular attention to the inside of Sam’s elbow, possibly his favorite spot in the world from now on, Sam clears his throat. “Uh…Dean? Not that this ain’t uh…but do you intend to get this show on the road sometime today?” He jerks his chin towards his crotch.  
  
Dean follows the motion with his eyes, somewhat nonplussed, until he notices that Sam’s erection has wilted considerably. How’s that even possible? Sam should be trembling with desire at this point, barely coherent, precome leaking from his cock. Instead, he’s just lying there, looking about as excited as he does examining dead bodies at the morgue. Actually, come to think of it, Dean’s seen him a good deal more enthusiastic around corpses than he seems now.  
  
“Show me what you like,” he invites Sam, doing his best to work around his mortification. They’re both naked, sex is sex, and his memory foam is the most comfortable space in the universe—what could go wrong?  
  
Apparently, a lot.  
  
Sam flips them and suddenly his hands are everywhere like a friggin’ volcano. Shit, Dean’s gonna be bruised all over tomorrow.  
  
A slick finger pushes into his entrance. How did Sam get to the lube out so damn fast—ugh, is that _spit_? Dean’s barely finished that thought when finger number two joins the first. The burn is enough to distract him from his disgust.  
  
Shit, Sam. Someone really needs to teach that kid a thing or two about proper foreplay.  
  
Before Dean’s had time to adjust to the stretch, Sam withdraws both fingers with a wet plop. A moment later something bigger nudges against his ass—fuck, is that Sam’s cock?  
  
“You gotta be kidding me!” He flexes both thighs and shoves. Possibly with a little more force than necessary. There’s a dull thud—shit, did he just kick his little brother off the bed?  
  
He glances down at Sam, who thankfully just seems thoroughly confused, but unharmed. “Sammy, you okay?”  
  
“I could ask you the same thing,” Sam says, climbing back on the bed.  
  
“I—what happened to foreplay?”  
  
“Dean, all we’ve done so far is foreplay!”  
  
“Oh.” Dean wipes a hand across his sweaty forehead. He’s feeling more embarrassed than aroused at this point, and one glance at Sam’s crotch tells him that he’s not the only one.  
  
But Dean’s never been one to give up easy. Or at all. He helped stop the apocalypse and lock the leviathans back in purgatory. He’s gonna succeed at having sex with his brother, too, and if it’s the last damn thing he does.  
  
“Watch this,” he says, lowering his voice to the gravelly drawl that always works like a charm, at least on the ladies. He retrieves a tube of K-Y from his bedside drawer, liberally coats his index finger and reaches behind him. For a few seconds, all he does is circle his hole. Then, letting his eyes fall shut, he slips it inside, exhaling a low moan.  
  
Beside him, he can hear Sam gasp. He cracks his eyes open a fraction. Sam’s biting his lip, his eyes trained on Dean’s ass with more focus than he’s ever devoted to any of their cases, and he’s got a hand wrapped around his dick. Thank hell. Looks like they’ve finally discovered something which works for both of them.  
  
Dean takes his time to prepare himself, fucking himself half-dizzy on his first finger before he adds a second, then a third. It’s addictive, having Sam’s eyes on him. He could come, just from this. But he’s got bigger plans for tonight, like _literally_ ; so he throws Sam the hooded gaze Lisa used to call his _million dollar hooker eyes_ and pants, “One more, Sammy, come on.”  
  
Sam sucks in a wet breath, and then he’s right there, his lube-slick finger sliding in next to Dean’s three. It’s intimate and perfect and hotter than anything Dean’s ever done before, Rhonda Hurley included.  
  
“Fuck.” Dean lets his head fall against Sam’s shoulder, feels Sam shudder in answer.  
  
“Dean, please, can I, can I?” Sam asks frantically, and Dean can only nod, thighs trembling with need.  
  
“Just go slow,” he murmurs as he sinks back onto the pillow.  
  
Eyes blown and tender, Sam positions himself at Dean’s entrance. Thanks to the thorough prep Dean’s body accepts him without resistance.  
  
And then Sam’s _inside_ him and Dean almost forgets to breathe. Technically, Sam’s always been inside him, because there ain’t a fiber in Dean’s body which doesn’t belong to Sam, but it’s overwhelming to have Sam acknowledge that, to fill all the spaces Dean carved out for him.  
  
Looming above Dean, biceps straining, so strong and beautiful, Sam rolls his hips, once, twice… After that Dean kinda loses track.  
  
The next thing he becomes aware of is the vaguely disgusting sensation of come cooling on his stomach, and the blissful heaviness of every limb.  
  
It takes him a little longer to realize that Sam’s dick is still inside him, still hard, still grinding.  
  
Wow, geekboy’s got stamina.  
  
For a while, Dean contents himself with running his fingers through Sam’s sweat-soaked hair, taking pride in his little brother’s outstanding performance. Eventually, though, the feeling of being pleasantly fucked-out dissipates, and all that remains is the sense of being fucked-out as in _sore as hell_.  
  
“Sam,” he whines. “You gonna come sometime this century?”  
  
“Sorry.” Sam looks honestly apologetic. “I’m trying. It’s just—I need more friction.”  
  
As far as Dean’s concerned, Sam’s got more than enough friction already, but whatever. “Just get on with it,” he grumbles.  
  
“Oh, Dean, you really know how to turn on a guy,” Sam scoffs, not unkindly, though with a hint of petulance. Which reminds Dean of how a little six-year-old Sammy sulked for a week when Dad forgot to buy them the ice cream he’d promised—and yeah, that’s not exactly the kind of mental image he wants to have when said no longer so little Sam splits open his ass with his humongous dick.  
  
Then Sam’s fingers dig into the flesh of Dean’s hips and he begins to pounds into Dean in earnest, and fuck, that hurts enough to drive all inappropriate images from Dean’s mind. If Dean thought Sam was an animal before—it’s nothing in comparison to what he’s doing now. Sam appears determined to find out if he can shove his cock back out through Dean’s throat.  
  
A particularly rough thrust sends Dean’s head banging against the headboard. Great. If he doesn’t die from internal organ failure, he’ll go out due to brain hemorrhage. In rare instances of absolute honesty he’s dared admit to himself that he’d prefer not to die with a gun in his hand but in his bed like a regular Joe the Plumber. This isn’t what he had in mind.  
  
But the impetus which probably cost Dean all his remaining brain cells finally gives Sam the friction he needs. With a groan he spills deep inside Dean.  
  
A minute later he pulls out—which fucking hurts!—and collapses on the mattress next to Dean.  
  
  
Dean sneaks a glance at him. Sam looks—well, Dean’s not exactly sure what he looks like. But he’s never seen that look on any of his previous partners. Not a good sign.  
  
“So,” he ventures.  
  
Sam blinks at him, licks his lips. “So,” he says.  
  
“That kinda sucked.”  
  
Sam snorts. “You think?”  
  
Maybe the total honestly policy ain’t so fabulabulicious after all. _Bull_ ’s more like it.  
  
Since Dean’s brain-to-mouth filter has never functioned particularly well, least of all in situations of shock, the next thing that comes out of his mouth is, “No wonder you never get laid, dude.”  
  
As soon as the words have left his mouth, Dean wants to disappear under his blankets and never emerge again. If Sam had killed him earlier with his monster cock, he’d have deserved it.  
  
Fortunately, Sam seems mostly amused. “Dean, I’ve fucked girls half your size twice as hard, and they didn’t even wince.”  
  
This time Dean manages to bite back the first response which comes to mind. Good thing, too, since it’s, _That’s cause they weren’t girls but monsters._  
  
Instead, he asks, sobering, “So what now?” He hadn’t meant it to come out quite so insecure.  
  
Sam’s a good guy. The best. He said he wants to spend his life with Dean. He’s not just gonna leave ‘cause the sex is crappy, Dean’s pretty sure. Like, really pretty sure. But he can’t be absolutely certain until he’s asked.  
  
“Dean.” Sam’s wearing the intense, soul-searching look he usually reserves for traumatized witnesses. Dean’s not quite sure whether to be pleased or offended. “When I said that you’re it for me, I didn’t mean just because you’re a great lay.” He swallows, a flash of dimples. “I admit, I was hoping you’d be a bit more…But we can practice, right? Just think of Cas. He was a pretty awful hunter at first, but now he’s halfway decent.”  
  
Dean gapes at his brother. “Dude, you _did not_ just compare having sex with me to Cas’s craptastic first steps as a hunter?”  
  
He’s ready to punch him when he sees that Sam’s laughing. The fucker.  
  
And okay, maybe Dean’s laughing too.  
  
For the first time that evening, Dean feels truly at ease, no trace of awkwardness left. He’s even beginning to remember why he thought this was such a fantastic idea to begin with. He and Sam—they just click. They’re good together. Comfortable.  
  
Still laughing, he collapses across Sam’s chest. He can feel Sam’s laughter bubbling underneath his skin. It’s kinda awesome.  
  
“We need a shower,” Sam remarks at some point.  
  
“Yeah,” Dean agrees. Sam’s come is oozing out of his ass, which is seriously gross. Plus his own come is still sticking to his chest, dried and flaky.  
  
He doesn’t move.  
  
“You gonna move sometime?” Sam asks.  
  
“Nah,” Dean mumbles. “I think you broke my back.”  
  
“You’re such a baby,” Sam replies, voice nothing but fond, and wraps his arms around Dean.  
  
As Dean twists his head to press a kiss to the corner of Sam’s mouth, he can’t help but think that while they might still have to work on the awesome sex part, they’re already pretty awesome when it comes to cuddling.

**Author's Note:**

> Thanks for reading. Feedback is love.
> 
> You can also talk to me here: [LJ](http://frozen-delight.livejournal.com/) | [Tumblr](http://frozen-delight.tumblr.com/)


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